JP6404938B2 - 二量体アニオン性モノアゾ染料 - Google Patents
二量体アニオン性モノアゾ染料 Download PDFInfo
- Publication number
- JP6404938B2 JP6404938B2 JP2016553509A JP2016553509A JP6404938B2 JP 6404938 B2 JP6404938 B2 JP 6404938B2 JP 2016553509 A JP2016553509 A JP 2016553509A JP 2016553509 A JP2016553509 A JP 2016553509A JP 6404938 B2 JP6404938 B2 JP 6404938B2
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- JP
- Japan
- Prior art keywords
- och
- hydrogen
- alkyl
- branched
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- 239000000539 dimer Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 104
- 229910052739 hydrogen Inorganic materials 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
- 238000004043 dyeing Methods 0.000 claims description 43
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 40
- 239000000758 substrate Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 150000002431 hydrogen Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 28
- 238000007639 printing Methods 0.000 claims description 22
- -1 -SO 3 H Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000004952 Polyamide Substances 0.000 claims description 16
- 229920002647 polyamide Polymers 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 12
- 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 239000002657 fibrous material Substances 0.000 claims description 7
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 238000001179 sorption measurement Methods 0.000 claims description 5
- 229920001410 Microfiber Polymers 0.000 claims description 4
- 238000010014 continuous dyeing Methods 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003658 microfiber Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000007447 staining method Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 10
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000003107 substituted aryl group Chemical group 0.000 description 10
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 210000002268 wool Anatomy 0.000 description 8
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000004753 textile Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 3
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 3
- 239000000980 acid dye Substances 0.000 description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000001044 red dye Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
- 240000008886 Ceratonia siliqua Species 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 239000001048 orange dye Substances 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- OMQCGHBXGJBBOL-UHFFFAOYSA-N 2-amino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=CC=C1S(O)(=O)=O OMQCGHBXGJBBOL-UHFFFAOYSA-N 0.000 description 1
- FJHGMUDVUAXUEK-UHFFFAOYSA-N 2-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(N)=C1 FJHGMUDVUAXUEK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241001416177 Vicugna pacos Species 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000085 cashmere Anatomy 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 210000000050 mohair Anatomy 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/205—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14000669.3 | 2014-02-25 | ||
| EP14000669.3A EP2910608B1 (en) | 2014-02-25 | 2014-02-25 | Dimeric anionic monoazo dyes |
| PCT/EP2015/000425 WO2015128081A1 (en) | 2014-02-25 | 2015-02-24 | Dimeric anionic monoazo dyes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017512227A JP2017512227A (ja) | 2017-05-18 |
| JP2017512227A5 JP2017512227A5 (es) | 2017-08-10 |
| JP6404938B2 true JP6404938B2 (ja) | 2018-10-17 |
Family
ID=50184718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016553509A Active JP6404938B2 (ja) | 2014-02-25 | 2015-02-24 | 二量体アニオン性モノアゾ染料 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP2910608B1 (es) |
| JP (1) | JP6404938B2 (es) |
| KR (1) | KR102321493B1 (es) |
| CN (1) | CN106068308B (es) |
| ES (1) | ES2638566T3 (es) |
| MX (1) | MX366626B (es) |
| PT (1) | PT2910608T (es) |
| TW (1) | TWI631187B (es) |
| WO (1) | WO2015128081A1 (es) |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2335137A (en) * | 1943-11-23 | Diamino ddyhenyl methanes | ||
| DE2606560A1 (de) * | 1976-02-19 | 1977-08-25 | Behringwerke Ag | Indikatoren |
| CH654321A5 (de) * | 1981-02-20 | 1986-02-14 | Ciba Geigy Ag | Disazofarbstoffe und ihre verwendung in farbphotographischen aufzeichnungsmaterialien fuer das silberfarbbleichverfahren. |
| JP2853351B2 (ja) * | 1990-11-07 | 1999-02-03 | 富士電機株式会社 | 電子写真用感光体 |
| TW225549B (es) * | 1992-04-14 | 1994-06-21 | Bayer Ag | |
| EP1753822B1 (en) * | 2004-05-19 | 2009-07-15 | Clariant Finance (BVI) Limited | Bridged monoazo dyes |
| PT2016135E (pt) | 2006-04-07 | 2009-08-17 | Clariant Finance Bvi Ltd | Corantes ácidos |
| US20090126128A1 (en) * | 2006-05-16 | 2009-05-21 | Clariant Finance (Bvi) Limited | Disazo Acid Dyes |
| WO2010010032A2 (en) | 2008-07-23 | 2010-01-28 | Ulrich Geiger | Acid dyes |
| EP2163587A1 (en) * | 2008-09-11 | 2010-03-17 | Clariant International Ltd. | Acid dyes |
| TWI561588B (en) | 2011-10-22 | 2016-12-11 | Archroma Ip Gmbh | Trisazo acid dyes |
-
2014
- 2014-02-25 EP EP14000669.3A patent/EP2910608B1/en active Active
- 2014-02-25 PT PT140006693T patent/PT2910608T/pt unknown
- 2014-02-25 ES ES14000669.3T patent/ES2638566T3/es active Active
-
2015
- 2015-01-23 TW TW104102312A patent/TWI631187B/zh active
- 2015-02-24 WO PCT/EP2015/000425 patent/WO2015128081A1/en active Application Filing
- 2015-02-24 MX MX2016010932A patent/MX366626B/es active IP Right Grant
- 2015-02-24 JP JP2016553509A patent/JP6404938B2/ja active Active
- 2015-02-24 CN CN201580010331.6A patent/CN106068308B/zh active Active
- 2015-02-24 KR KR1020167026177A patent/KR102321493B1/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| KR102321493B1 (ko) | 2021-11-03 |
| JP2017512227A (ja) | 2017-05-18 |
| ES2638566T3 (es) | 2017-10-23 |
| PT2910608T (pt) | 2017-08-30 |
| CN106068308A (zh) | 2016-11-02 |
| KR20160124879A (ko) | 2016-10-28 |
| CN106068308B (zh) | 2017-11-03 |
| WO2015128081A1 (en) | 2015-09-03 |
| EP2910608B1 (en) | 2017-05-31 |
| TW201542705A (zh) | 2015-11-16 |
| MX366626B (es) | 2019-07-17 |
| MX2016010932A (es) | 2017-04-25 |
| EP2910608A1 (en) | 2015-08-26 |
| TWI631187B (zh) | 2018-08-01 |
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